Meet Tommy Reamon of CITY ON MY CHEST

Today we’d like to introduce you to Tommy Reamon.

Hi Tommy , we’re thrilled to have a chance to learn your story today. So, before we get into specifics, maybe you can briefly walk us through how you got to where you are today?
I grew up in Newport News, Virginia, where football and community were everyday language. My father, Coach Tommy Reamon Sr., molded NFL quarterbacks and generations of young men, so I learned early that winning wasn’t just about the scoreboard—it was about leadership, discipline, and service. As a nationally ranked high-school quarterback who went on to play in college, I carried that standard into every locker room I entered.

After college, I shifted to the other side of the whistle—scouting and personnel. I cut my teeth with the Pittsburgh Steelers and New Orleans Saints, learning how to evaluate talent, build rosters, and spot the hidden traits that translate on Saturdays and Sundays. Those years taught me two truths: details decide everything, and character is a skill. I later brought those lessons home, coaching and supporting programs in Virginia, and working at the intersection of recruiting, player development, and program culture. Today, I still live in the film room and the community—helping student-athletes grow on the field while preparing them for life beyond it.

That same spirit birthed my brand, City On My Chest—a movement disguised as apparel. What began as a local T-shirt became a platform to celebrate hometown pride and invest back into the neighborhoods that raised us. We opened a retail store in Patrick Henry Mall, surpassed $4.2M in lifetime sales, and sold over 100,000 shirts nationwide—more than 60,000 of them Virginia-themed. But the real impact happens off the sales sheet: through our nonprofit Uplift Your City Foundation, we host youth mentorships, pep rallies, sports camps, entrepreneur seminars, and our free community festival, City Fest. The brand’s message is simple: greatness can come from anywhere—and we prove it together.

Today my life is a blend of film study, practice schedules, design meetings, and community events. I’m building media and education tools for athletes and families, launching new initiatives like scouting platforms for athletes , and partnering with schools and cities to expand opportunity. Football gave me a blueprint—prepare relentlessly, lead from the front, and make your teammates better. Entrepreneurship gave me a vehicle to scale that impact. My mission is to keep opening doors so the next kid from our city doesn’t have to ask if it’s possible—he can point to home and say, “Watch me.”

Alright, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
Not at all—and I wouldn’t want it any other way. My path has been full of lessons disguised as obstacles. In football, I learned early that adversity doesn’t build character—it reveals it. Whether it was fighting for a roster spot, transitioning from player to coach, or getting told “no” more times than I could count, every setback forced me to adjust, not quit.

When I stepped into entrepreneurship, those same lessons showed up again—except this time, there was no playbook. I went from designing shirts in my bedroom to running a full retail store, managing staff, learning manufacturing, marketing, taxes, and supply chains—all while keeping the mission at the center. There were nights I questioned if it was worth it, but every time I saw a young person wearing City On My Chest with pride, it reminded me why I started.

Building a business and a brand rooted in community isn’t easy—it’s emotional, unpredictable, and personal. But the struggle made the purpose stronger. Every challenge sharpened me as a leader, as a man, and as a father. The road wasn’t smooth, but it’s been real—and that’s where the growth came from.

Great, so let’s talk business. Can you tell our readers more about what you do and what you think sets you apart from others?
City On My Chest is more than a clothing brand—it’s a movement that represents pride, purpose, and community. We specialize in high-quality, city-themed apparel that celebrates where people come from and reminds them that greatness can rise from anywhere. Every design carries that message, turning local pride into a national statement.

We’ve sold over 100,000 shirts across the country, with more than 60,000 right here in Virginia. But what sets us apart isn’t just the numbers—it’s the impact behind the brand. Through our nonprofit, Uplift Your City Foundation, we reinvest back into the same communities that support us. We host free youth mentorship programs, pep rallies, sports camps, entrepreneur seminars, and our annual City Fest, which brings thousands of families together every year.

What I’m most proud of is seeing our logo—the words “City On My Chest”—worn by everyday people, local leaders, and even elected officials as a badge of unity. The brand has become a symbol of hope and representation for Virginia, showing the next generation that you can take pride in your city and still dream beyond it.

Our focus goes far beyond apparel. We’re building a platform that merges culture, sports, and community impact—offering creative collaborations, mentorship, and storytelling that inspire others to lead. For us, it’s not just about what you wear; it’s about what you stand for.

When people see “City On My Chest,” I want them to feel seen, inspired, and reminded that the power to create change starts right where they are.

Is there any advice you’d like to share with our readers who might just be starting out?
My biggest advice is simple—start where you are, and build from there. Don’t wait until everything feels perfect. When I started City On My Chest, I didn’t have investors, a business degree, or a blueprint. I just had belief, purpose, and consistency. The key is to move with intent—you’ll figure out the rest along the way.

I wish I knew earlier that success doesn’t come from trying to skip steps—it comes from respecting the process. Every late night, every failure, every adjustment is teaching you something that shortcuts never will.

Also, protect your vision. Everyone won’t understand it right away, and that’s okay. You’re not building for validation—you’re building for impact. Whether it’s sports, business, or life, stay disciplined, stay humble, and keep showing up.

And remember this: momentum starts small. You don’t need the whole world to believe in you—you just need to prove yourself right, one day at a time.

Contact Info:

• Website: https://www.cityonmychest.com
• Instagram: https://www.instagram.com/cityonmychest
• LinkedIn: https://www.linkedin.com/in/tommy-reamon-jr-278623b1